Donald Trump is very proud of himself for forcing President Obama to release his birth certificate, ending the debate over whether he was legally fit to lead the country. But not everything the Donald has put his name behind has succeeded. TIME takes a look at some gambles that went bust

Trump Airlines

By Kayla WebleyFriday, Apr. 29, 2011

David A. Cantor / AP

In October 1988, Donald Trump threw his wallet into the airline business by purchasing Eastern Air Shuttle, a service that for 27 years had run hourly flights between Boston, New York City and Washington, D.C. For roughly $365 million, Trump got a fleet of 17 Boeing 727s, landing facilities in each of the three cities and the right to paint his name on an airplane. Trump pushed to give the airline the Trump touch, making the previously no-muss, no-fuss shuttle service into a luxury experience. To this end, he added maple-wood veneer to the floors, chrome seat-belt latches and gold-colored bathroom fixtures. But his gamble was a bust. A lack of increased interest from customers (who favored the airline for its convenience not its fancy new look) combined with high preGulf War fuel prices meant the shuttle never turned a profit. The high debt forced Trump to default on his loans, and ownership of the company was turned over to creditors. The Trump Shuttle ceased to exist in 1992 when it was merged into a new corporation, Shuttle Inc. No word on whether the gold-plated faucets survived the merger.